23530-41-8Relevant articles and documents
One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
supporting information, p. 6127 - 6140 (2021/07/21)
A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
Tweaking Subtype Selectivity and Agonist Efficacy at (S)-2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propionic acid (AMPA) Receptors in a Small Series of BnTetAMPA Analogues
Wang, Shuang-Yan,Larsen, Younes,Navarrete, Cristina Vara,Jensen, Anders A.,Nielsen, Birgitte,Al-Musaed, Ali,Frydenvang, Karla,Kastrup, Jette Sandholm,Pickering, Darryl S.,Clausen, Rasmus Pr?torius
supporting information, p. 2244 - 2254 (2016/03/25)
A series of analogues of the (S)-2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propionic acid (AMPA) receptor agonist BnTetAMPA (5b) were synthesized and characterized pharmacologically in radioligand binding assays at native and cloned AMPA receptors and functionally by two-electrode voltage clamp electrophysiology at the four homomeric AMPA receptors expressed in Xenopus laevis oocytes. The analogues 6 and 7 exhibit very different pharmacological profiles with binding affinity preference for the subtypes GluA1 and GluA3, respectively. X-ray crystal structures of three ligands (6, 7, and 8) in complex with the agonist binding domain (ABD) of GluA2 show that they induce full domain closure despite their low agonist efficacies. Trp767 in GluA2 ABD could be an important determinant for partial agonism of this compound series at AMPA receptors, since agonist efficacy also correlated with the location of the Trp767 side chain.
Nickel-catalyzed regio- and enantioselective annulation reactions of 1,2,3,4-benzothiatriazine-1,1(2H)-dioxides with allenes
Miura, Tomoya,Yamauchi, Motoshi,Kosaka, Akira,Murakami, Masahiro
supporting information; experimental part, p. 4955 - 4957 (2010/10/02)
(Figure Presented) Extrusion of N2:1,2,3,4-Benzothiatriazine1,1 (2H)-dioxides reacted with alienes in the presence of a nickel (0)/(R)-quinap complex to produce a variety of substituted 3,4-dihydro-1,2-benzothiazine1,1 (2H)-dioxides in a regio- and enantioselective fashion. An intermediate nickelacycle was generated through denitrogenative activation of the triazo moiety which allowed the intermolecular incorporation of an aliene group. quinap = 1-(2diphenylphosphino-1-naphthyl)isoquinoline.